Portland to Hood River is an approximately 1.5-hour car ride. You can also take a bus; or take a train. December in Hood River sees daily highs of 42°F and lows of 35°F at night. Wrap up your sightseeing on the 10th (Sun) early enough to travel to Fort Collins.

Do a combination of bus and flight from Hood River to Fort Collins in 8.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Hood River to Fort Collins is 1 hour. Traveling from Hood River in December, plan for slightly colder nights in Fort Collins, with lows around 17°F. On the 13th (Wed), you'll have the morning to explore before heading off to Milwaukee.

Traveling by combination of bus and flight from Fort Collins to Milwaukee takes 7.5 hours. Alternatively, you can drive; or do a combination of bus and train. The time zone difference moving from Mountain Standard Time to Central Standard Time is 1 hour. When traveling from Fort Collins in December, plan for slightly colder days and about the same nights in Milwaukee: temperatures range from 34°F by day to 21°F at night. Finish your sightseeing early on the 15th (Fri) so you can travel back home.